ChemicalBook > CAS DataBase List > N-BOC-3-AMINOPHENOL

N-BOC-3-AMINOPHENOL

Product Name: N-BOC-3-AMINOPHENOL
CAS No.: 19962-06-2
Chemical Name: N-BOC-3-AMINOPHENOL
Synonyms: 3-(Boc-amino)phenol;Neostigmine Impurity 12;N-Boc-3-aMinophenol 97%;N-Boc-3-aminophenol;Neostigmine bromide Impurity V;tert-butyl N-(3-hydroxyphenyl)carbamate;Carbamic acid,N-(3-hydroxyphenyl)-, 1,1-dimethylethyl ester
CBNumber: CB2972550
Molecular Formula: C11H15NO3
Formula Weight: 209.24
MOL File: 19962-06-2.mol

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N-BOC-3-AMINOPHENOL Property

Melting point:: 134-138 °C(lit.)
Boiling point:: 286.8±23.0 °C(Predicted)
Density: 1.182±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
form: solid
pka: 9.69±0.10(Predicted)
Appearance: White to off-white Solid
InChI: InChI=1S/C11H15NO3/c1-11(2,3)15-10(14)12-8-5-4-6-9(13)7-8/h4-7,13H,1-3H3,(H,12,14)
InChIKey: HJQNVUQTARSZDK-UHFFFAOYSA-N
SMILES: C(OC(C)(C)C)(=O)NC1=CC=CC(O)=C1

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Safety

Hazard Codes: Xi
Risk Statements: 43
Safety Statements: 26-36/37
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H317May cause an allergic skin reaction
Precautionary statements: P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 635952
Product name: N-Boc-3-aminophenol
Purity: 97%
Packaging: 5g
Price: $75.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: 635952
Product name: N-Boc-3-aminophenol
Purity: 97%
Packaging: 25g
Price: $402
Updated: 2023/06/20

TCI Chemical

Product number: B6210
Product name: tert-Butyl (3-Hydroxyphenyl)carbamate
Packaging: 1G
Price: $38
Updated: 2025/07/31

TCI Chemical

Product number: B6210
Product name: tert-Butyl (3-Hydroxyphenyl)carbamate
Packaging: 5G
Price: $113
Updated: 2025/07/31

TRC

Product number: T135558
Product name: tert-Butyl3-Hydroxyphenylcarbamate
Packaging: 100mg
Price: $75
Updated: 2021/12/16

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N-BOC-3-AMINOPHENOL Chemical Properties,Usage,Production

Synthesis

24424-99-5

591-27-5

19962-06-2

General steps: 1. 3-Aminophenol (1 g, 9.16 mmol, 1.0 eq.) was dissolved in THF (35 mL) and a solution of di-tert-butyl dicarbonate (2.41 g, 11.1 mmol, 1.2 eq.) in THF (10 mL) was slowly added. The reaction mixture was refluxed overnight and the solvent was evaporated under vacuum to give a brown residue. 2. The residue was dissolved in EtOAc, washed sequentially with H2O, saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuum to give the carbamate derivative as a gray solid in quantitative yield. 3. Imidazole (1.37 g, 20.1 mmol, 2.0 eq.) was slowly added to a solution of DMF (15 ml) of the above solid (2.11 g, 10.0 mmol, 1.0 eq.) at 0 °C, followed by a solution of DMF (5 ml) of TBSCl (1.75 g, 11.6 mmol, 1.15 eq.). After stirring at room temperature overnight, the reaction mixture was partitioned between half-saturated NaHCO3 solution and AcOEt. The organic layer was washed sequentially with half-saturated and NH4Cl solution, saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuum to give the di-protected compound (2.89 g, 89%) as a white solid. 4. The above compound (500 mg, 1.54 mmol, 1.0 eq.) was dissolved in freshly distilled ether (15 ml) and a pentane [1.6 M] solution of tert-butyllithium (2.31 ml, 3.71 mmol, 2.4 eq.) was added at 40 °C and stirred for 2 hours. DMF (0.95 ml, 12.36 mmol, 8.0 eq.) was then injected and the reaction mixture was warmed to 0 °C and stirred for 1 hour. The reaction mixture was partitioned between water and ether and the aqueous layer was extracted three times with ether. The combined organic layers were washed twice with brine, dried over MgSO4 and concentrated in vacuum and purified by column chromatography (petroleum ether/ether, 99:1) to give the formylated product (239 mg, 44%) as a white powder. 5. Potassium fluoride (140.4 mg, 2.42 mmol, 2.2 eq.) was added to a solution of the above formylated product (386.2 mg, 1.099 mmol, 1.0 eq.) in DMF (30.9 ml), followed by benzyl bromide (0.17 ml, 1.43 mmol, 1.3 eq.). After stirring at room temperature overnight, the reaction mixture was diluted in water and AcOEt and the aqueous layer was extracted twice with AcOEt. The combined organic layers were sequentially washed twice with 0.5 M HCl solution, once with water, twice with LiCl (20%) solution and brine, dried over MgSO4 and then concentrated in vacuum to quantitatively obtain the O-benzyl derivative (351.3 mg) as a white powder. 6. The O-benzyl derivative (351.3 mg, 1.073 mmol, 1.0 eq.) was dissolved in ethanol (4.3 ml), diethyl malonate (0.4 ml, 2.68 mmol, 2.5 eq.), piperidine (0.26 ml, 2.7 mmol, 2.5 eq.) and acetic acid (0.006 ml, 0.107 mmol, 0.1 equivalent). After refluxing and stirring overnight, the mixture was cooled to 5 °C, the precipitate was filtered and washed with cold ethanol (20 °C) to give the quinolinone product (198 mg, 57%). 7. K2CO3 (2 eq.) and LiI (20-25 mol%) were added to a solution of quinolinone derivatives (1 eq.) in DMSO (1.5 ml/mmol), followed by alkyl halide (1.2 eq.). After reflux heating overnight, the reaction mixture was partitioned between water and DCM and the aqueous layer was extracted three times with DCM. The combined organic layers were washed with water, dried over MgSO4 and concentrated in vacuum. 8. The ester product (1 eq.) was dissolved in THF (6 ml/mmol) and a solution of LiOH (10 eq.) in water (6 ml/mmol) was added. The mixture was stirred vigorously and heated at reflux for 1 hr 40 min before THF was removed by vacuum distillation. pH was adjusted to 2 with HCl (1 M), the white precipitate was diluted in AcOEt, and the aqueous layer was extracted with AcOEt three times. The combined organic layers were washed with water, dried over MgSO4 and concentrated in vacuum, and the crude product was recrystallized from ethanol to give a sample of sufficient purity for biological tests.

References

[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7107 - 7117
[2] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4259 - 4263
[4] Patent: WO2017/158612, 2017, A1. Location in patent: Page/Page column 25
[5] New Journal of Chemistry, 2018, vol. 42, # 12, p. 10142 - 10147

N-BOC-3-AMINOPHENOL Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-BOC-3-AMINOPHENOL manufacturers

Career Henan Chemical Co

Product: N-BOC-3-AMINOPHENOL 19962-06-2
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 100kg
Release date: 2020-01-14

19962-06-2, N-BOC-3-AMINOPHENOLRelated Search:

3-Dimethylaminoanisole m-(Methylamino)phenol 3-AMINOPHENYL N,N-DIMETHYLCARBAMATE, 97 tert-butyl 3-methoxyphenylcarbamate N-BOC-3-AMINOPHENOL TERT-BUTYL 4-(METHOXYCARBONYL)-3-METHOXYPHENYLCARBAMATE TERT-BUTYL 5-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE 2-TERT-BUTOXYCARBONYLAMINO-4,5-DIMETHOXY-BENZOIC ACID (2-AMINO-5-METHOXY-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER BOC-2-AMINO-3,4,5-TRIMETHOXYBENZOIC ACID 3-[(tert-Butoxycarbonyl)amino]-5-hydroxybenzoic acid TERT-BUTYL 7-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE tert-butyl 4-(aminomethyl)-3-(trifluoromethoxy)phenylcarbamate TERT-BUTYL 1,3-BENZODIOXOL-4-YLCARBAMATE 4-[(tert-butoxycarbonyl)amino]-2-hydroxybenzoic acid TERT-BUTYL (5-BROMO-1,3-BENZODIOXOL-4-YL)CARBAMATE TERT-BUTYL (5-CHLORO-1,3-BENZODIOXOL-4-YL)CARBAMATE Tert-butyl 2-(aminomethyl)-4,5-dimethoxyphenylcarbamate

N-Boc-3-aMinophenol 97%

Carbamic acid,N-(3-hydroxyphenyl)-, 1,1-dimethylethyl ester

tert-butyl N-(3-hydroxyphenyl)carbamate

Neostigmine bromide Impurity V

Neostigmine Impurity 12

<i>N</i>-Boc-3-aminophenol

3-(Boc-amino)phenol

19962-06-2

Organic Building Blocks

Oxygen Compounds

Phenols